1515-76-0 Usage
Description
1-Acetoxy-1,3-Butadiene (1-ABD) is a clear colorless to slightly yellow viscous liquid that can be generated by a potassium or sodium acetate catalyzed reaction between crotonaldehyde and acetic anhydride. The product is a mixture of cis and trans forms, which has been confirmed by its physical properties and IR spectra. It is also reported to be formed as a major product during the acetoxylation of 1,3-butadiene (BD) in the gas phase in the presence of a Pd-KOAc (palladium-potassium acetate) catalyst. 1-ABD participates as a 2Π or 4Π diene in cycloaddition reactions.
Uses
1. Used in Chemical Synthesis:
1-Acetoxy-1,3-Butadiene is used as a diene in various chemical reactions for the synthesis of different compounds. It is particularly useful in Diels-Alder reactions, which are important in the formation of cyclic compounds.
2. Used in Pharmaceutical Industry:
1-Acetoxy-1,3-Butadiene is used as a reactant in the synthesis of pharmaceutical compounds through intermolecular oxa-Pictet-Spengler cyclization, a reaction that contributes to the development of complex molecular structures.
3. Used in Polymer Industry:
1-Acetoxy-1,3-Butadiene is used as a monomer in the polymer industry for the production of various polymers with specific properties, such as rubber and plastics.
4. Used in Organic Chemistry Research:
1-Acetoxy-1,3-Butadiene is used as a reactant in organic chemistry research to study the reactivity and selectivity of different dienes and dienophiles in Diels-Alder reactions, as well as other cycloaddition reactions.
5. Used in the Synthesis of Fine Chemicals:
1-Acetoxy-1,3-Butadiene is used as a building block in the synthesis of fine chemicals, such as fragrances, dyes, and other specialty chemicals, due to its ability to participate in various cycloaddition reactions.
6. Used in the Synthesis of Chiral Compounds:
1-Acetoxy-1,3-Butadiene is used in enantioselective Diels-Alder reactions to produce chiral compounds, which are important in the pharmaceutical and agrochemical industries for their specific biological activities.
Safety Profile
Poison by inhalation. Moderatelytoxic by other routes. A skin irritant. Mutation datareported. When heated to decomposition it emits acridsmoke.
Purification Methods
The commercial sample is stabilised with 0.1% of p-tert-butylcatechol. If the material contains crotonaldehyde (by IR, used in its synthesis), it should be dissolved in Et2O, shaken with 40% aqueous sodium bisulfite, then 5% aqueous Na2CO3, water, dried (Na2SO4) and distilled several times in a vacuum through a Widmer [Helv Chim Acta 7 59 1924] (p 11) or Vigreux column (p 11) [Wicterle & Hudlicky Collect Czech Chem Commun 12 564 1947, Hagemeyer & Hull Ind Eng Chem 41 2920 1949]. [Beilstein 2 III 295.]
Check Digit Verification of cas no
The CAS Registry Mumber 1515-76-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,1 and 5 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1515-76:
(6*1)+(5*5)+(4*1)+(3*5)+(2*7)+(1*6)=70
70 % 10 = 0
So 1515-76-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+
1515-76-0Relevant articles and documents
Stereoselective Substituent Effects on Conrotatory Electrocyclic Reactions of Cyclobutenes
Kirmse, Wolfgang,Rondan, Nelson G.,Houk, K. N.
, p. 7989 - 7991 (1984)
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Danno,S. et al.
, p. 4809 - 4813 (1969)
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1 - - 1, 3 - Alkadiene acyloxy method (by machine translation)
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Paragraph 0025-0029, (2019/05/08)
- 1, 3 - Alkadiene 1 - acyloxy [to] a production method of a industrially useful. (1) Represented by the formula [a] α, β - unsaturated aldehyde reaction to produce the metal alkoxide [...] process is performed, the following formula (3) is reacted with a carboxylic acid anhydride [...] step - 1, 3 - alkadiene represented by the preparation of 1 - acyloxy. (In formula (1), R1 - R3 The, each independently hydrogen, an alkyl group or the like. )[Drawing] no (by machine translation)
METHOD FOR PRODUCING 1-ACYLOXY-1,3-BUTADIENE
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Paragraph 0023, (2018/09/11)
PROBLEM TO BE SOLVED: To provide a method for producing a 1-acyloxy-1,3-butadiene that can be performed only with a base of a catalytic amount even when a substrate has a boiling point less than 135°C. SOLUTION: A method for producing a 1-acyloxy-1,3-butadiene represented by formula (3) includes treating α,β-unsaturated aldehyde with carboxylic acid anhydride and a catalytic amount of 4-dialkylaminopyridine at a temperature less than 135°C, without requiring a base other than 4-dialkylaminopyridine (R1-R2 independently represent H, a C1-30 linear/branched alkyl; R3 is H, a C1-30 alkyl or a C2-30 alkenyl; R4 is a C1-20 alkyl; alkyl groups of R3 and R4 may be linear/branched, substituted/unsubstituted with halogen, and the alkenyl group may further contain one or more C=C bonds in the group and may be linear/branched, substituted/unsubstituted with halogen). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity
B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg
supporting information, p. 2524 - 2532 (2014/11/08)
A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.
